diff --git a/lib/src/main/java/xyz/gianlu/librespot/core/Session.java b/lib/src/main/java/xyz/gianlu/librespot/core/Session.java
index 9b6da97c..6a37d70c 100644
--- a/lib/src/main/java/xyz/gianlu/librespot/core/Session.java
+++ b/lib/src/main/java/xyz/gianlu/librespot/core/Session.java
@@ -56,6 +56,8 @@
 import javax.crypto.Cipher;
 import javax.crypto.Mac;
 import javax.crypto.spec.SecretKeySpec;
+import javax.net.SocketFactory;
+import javax.net.ssl.SSLSocketFactory;
 import javax.xml.parsers.DocumentBuilder;
 import javax.xml.parsers.DocumentBuilderFactory;
 import javax.xml.parsers.ParserConfigurationException;
@@ -156,6 +158,10 @@ public Request authenticate(Route route, @NotNull Response response) {
                     }
                 });
             }
+            if (conf.proxyType == Proxy.Type.HTTP && conf.proxySSL) {
+                // builder.socketFactory(SSLSocketFactory.getDefault()) throws an error on some okhttp versions
+                builder.socketFactory(new DelegatingSocketFactory(SSLSocketFactory.getDefault()));
+            }
         }
 
         builder.addInterceptor(chain -> {
@@ -1029,6 +1035,7 @@ public final static class Configuration {
         // Proxy
         public final boolean proxyEnabled;
         public final Proxy.Type proxyType;
+        public final boolean proxySSL;
         public final String proxyAddress;
         public final int proxyPort;
         public final boolean proxyAuth;
@@ -1054,13 +1061,15 @@ public final static class Configuration {
         // Network
         public final int connectionTimeout;
 
-        private Configuration(boolean proxyEnabled, Proxy.Type proxyType, String proxyAddress, int proxyPort, boolean proxyAuth, String proxyUsername, String proxyPassword,
+        private Configuration(boolean proxyEnabled, Proxy.Type proxyType, boolean proxySSL, String proxyAddress,
+                              int proxyPort, boolean proxyAuth, String proxyUsername, String proxyPassword,
                               TimeProvider.Method timeSynchronizationMethod, int timeManualCorrection,
                               boolean cacheEnabled, File cacheDir, boolean doCacheCleanUp,
                               boolean storeCredentials, File storedCredentialsFile,
                               boolean retryOnChunkError, int connectionTimeout) {
             this.proxyEnabled = proxyEnabled;
             this.proxyType = proxyType;
+            this.proxySSL = proxySSL;
             this.proxyAddress = proxyAddress;
             this.proxyPort = proxyPort;
             this.proxyAuth = proxyAuth;
@@ -1081,6 +1090,7 @@ public static final class Builder {
             // Proxy
             private boolean proxyEnabled = false;
             private Proxy.Type proxyType;
+            private boolean proxySSL = false;
             private String proxyAddress;
             private int proxyPort;
             private boolean proxyAuth;
@@ -1119,6 +1129,11 @@ public Builder setProxyType(Proxy.Type proxyType) {
                 return this;
             }
 
+            public Builder setProxySSL(boolean proxySSL) {
+                this.proxySSL = proxySSL;
+                return this;
+            }
+
             public Builder setProxyAddress(String proxyAddress) {
                 this.proxyAddress = proxyAddress;
                 return this;
@@ -1191,7 +1206,8 @@ public Builder setConnectionTimeout(int connectionTimeout) {
 
             @NotNull
             public Configuration build() {
-                return new Configuration(proxyEnabled, proxyType, proxyAddress, proxyPort, proxyAuth, proxyUsername, proxyPassword,
+                return new Configuration(proxyEnabled, proxyType, proxySSL, proxyAddress, proxyPort, proxyAuth,
+                        proxyUsername, proxyPassword,
                         timeSynchronizationMethod, timeManualCorrection,
                         cacheEnabled, cacheDir, doCacheCleanUp,
                         storeCredentials, storedCredentialsFile,
@@ -1245,7 +1261,12 @@ static ConnectionHolder create(@NotNull String addr, @NotNull Configuration conf
 
             switch (conf.proxyType) {
                 case HTTP:
-                    Socket sock = new Socket(conf.proxyAddress, conf.proxyPort);
+                    Socket sock;
+                    if (conf.proxySSL) {
+                        sock = SSLSocketFactory.getDefault().createSocket(conf.proxyAddress, conf.proxyPort);
+                    } else{
+                        sock = new Socket(conf.proxyAddress, conf.proxyPort);
+                    }
                     OutputStream out = sock.getOutputStream();
                     DataInputStream in = new DataInputStream(sock.getInputStream());
 
@@ -1264,7 +1285,7 @@ static ConnectionHolder create(@NotNull String addr, @NotNull Configuration conf
                         // Read all headers
                     }
 
-                    LOGGER.info("Successfully connected to the HTTP proxy.");
+                    LOGGER.info(String.format("Successfully connected to the %s proxy.", conf.proxySSL ? "HTTPS" : "HTTP"));
                     return new ConnectionHolder(sock);
                 case SOCKS:
                     if (conf.proxyAuth) {
@@ -1399,4 +1420,50 @@ public void run() {
             LOGGER.trace("Session.Receiver stopped");
         }
     }
+
+    /**
+     * A {@link SocketFactory} that delegates calls. Sockets can be configured after creation by
+     * overriding {@link #configureSocket(java.net.Socket)}.
+     *
+     * Copy/pasted from okhttp3 tests sources for HTTPS proxy support
+     */
+    public static class DelegatingSocketFactory extends SocketFactory {
+      private final SocketFactory delegate;
+
+      public DelegatingSocketFactory(SocketFactory delegate) {
+        this.delegate = delegate;
+      }
+
+      @Override public Socket createSocket() throws IOException {
+        Socket socket = delegate.createSocket();
+        return configureSocket(socket);
+      }
+
+      @Override public Socket createSocket(String host, int port) throws IOException {
+        Socket socket = delegate.createSocket(host, port);
+        return configureSocket(socket);
+      }
+
+      @Override public Socket createSocket(String host, int port, InetAddress localAddress,
+          int localPort) throws IOException {
+        Socket socket = delegate.createSocket(host, port, localAddress, localPort);
+        return configureSocket(socket);
+      }
+
+      @Override public Socket createSocket(InetAddress host, int port) throws IOException {
+        Socket socket = delegate.createSocket(host, port);
+        return configureSocket(socket);
+      }
+
+      @Override public Socket createSocket(InetAddress host, int port, InetAddress localAddress,
+          int localPort) throws IOException {
+        Socket socket = delegate.createSocket(host, port, localAddress, localPort);
+        return configureSocket(socket);
+      }
+
+      protected Socket configureSocket(Socket socket) throws IOException {
+        // No-op by default.
+        return socket;
+      }
+    }
 }
diff --git a/player/src/main/java/xyz/gianlu/librespot/player/FileConfiguration.java b/player/src/main/java/xyz/gianlu/librespot/player/FileConfiguration.java
index 58a2fd58..bec3e136 100644
--- a/player/src/main/java/xyz/gianlu/librespot/player/FileConfiguration.java
+++ b/player/src/main/java/xyz/gianlu/librespot/player/FileConfiguration.java
@@ -411,6 +411,7 @@ public Session.Configuration toSession() {
                 .setTimeManualCorrection(config.get("time.manualCorrection"))
                 .setProxyEnabled(config.get("proxy.enabled"))
                 .setProxyType(config.getEnum("proxy.type", Proxy.Type.class))
+                .setProxySSL(config.get("proxy.ssl"))
                 .setProxyAddress(config.get("proxy.address"))
                 .setProxyPort(config.get("proxy.port"))
                 .setProxyAuth(config.get("proxy.auth"))
diff --git a/player/src/main/resources/default.toml b/player/src/main/resources/default.toml
index d330fa94..266220a7 100644
--- a/player/src/main/resources/default.toml
+++ b/player/src/main/resources/default.toml
@@ -58,6 +58,7 @@ host = "0.0.0.0" # API listen interface (`api` module only)
 [proxy] ### Proxy ###
 enabled = false # Whether the proxy is enabled
 type = "HTTP" # The proxy type (HTTP, SOCKS)
+ssl = false # Connect to proxy using SSL (HTTP only)
 address = "" # The proxy hostname
 port = 0 # The proxy port
 auth = false # Whether authentication is enabled on the server